Water → 5-bromo-3-(1-{[2-(methyloxy)ethyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 1805889Notes

Reaction equation

HRID 1805889 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].Cl.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.O>CN(C)C=O.C(N(CC)CC)C>[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:23]1[CH2:28][CH2:27][N:26]([S:5]([CH2:4][CH2:3][O:2][CH3:1])(=[O:7])=[O:6])[CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 962WaterHCID 134802212-Methoxyethane-1-sulfonyl chlorideHCID 667232845-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride2×

Product 1

HCID 596006625-bromo-3-(1-{[2-(methyloxy)ethyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Under nitrogen, 2-(methyloxy)ethanesulfonyl chloride (43.8 g) was added dropwise over 30 minutes to a cooled, 10° C., suspension of 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride (Intermediate 1, 66 g) in N,N-dimethylformamide (DMF) (350 mL) and triethylamine (77 mL). The reaction mixture was stirred for 3 hours. The reaction mixture was poured into water (2000 mL) and stirred for 1 hour. The resultant solid was collected by filtration and washed with water. The solid was dried in vacuo at 40° C. to give the title compound (67.1 g) as a cream solid.

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water
  4. customThe solid was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-ce327f93e1fc4a6399402e3d6ee288a8
Source dataset
uspto-grants-2013_01
Patent number
US08354539B2

Reaction notes

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